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The Case for Staying Put

Ticking off destinations on your bucket list can be satisfying, but some travelers take comfort in returning to the same place, at the same time, year after year

Every month, another magazine arrives in the mail, and a new set of “It” destinations are anointed: Myanmar is the new Thailand! The Silk Road is the new Grand Tour! Just keeping the global nomad’s map straight can be exhausting.

And while getting there before Beyoncé can be exhilarating to some, others find comfort in a different sort of holiday. In a world where time is a luxury and your backstory—thanks to Google or the Ashley Madison breach—is public knowledge, heading to a hotel where everyone and everything is exactly as you left it can be as soothing as a standing weekly therapy session. Even for those who could easily spin the globe and choose any private resort, anywhere from Georgia (the state) to Georgia (the country), indulgence comes not from being the first or the most remote, but from knowing just which lounge chair secures the last rays of sun and what waiter will sneak you a second dessert. These “generational resorts” are comfort zones to annual guests; like the bar in Cheers, they are places where everybody knows their name. And that’s just how they like it.

Nostalgia has something to do with the desire to head back to the same spot every season. On Nantucket, the White Elephant hotel’s general manager, Bettina Landt, has seen this phenomenon for decades. “Our annual guests greatly value tradition and ease,” she says. “Parents who spent their childhood summers on the island with their family hope to create the same memories for their own children.” From generation to generation, ice cream at the Juice Bar, making sand castles at Jetties Beach and sneaking off with friends to the Chicken Box are all a part of growing up.

Carving out a week each year—the same time at the same place—often provides a light at the end of the tunnel (or, as was the case the past three years, at the end of a very dreary winter). At The Breakers, a 120-year-old resort in Palm Beach, annual visitors make up around 40 percent of the entire guest population from mid-December until the end of April. During peak holiday periods, that number rises to almost half. Regulars like financier Ben Jamron of New York City, who was married at The Breakers in 2007 and now comes back yearly, love that the guest rooms and public spaces retain their Old World glamour (the owners invest $25 million each year in refurbishments, which shows), but they also feel a kinship with the staff: 45 percent of the employees have worked at the patrician resort for at least five years and 20 staffers have been on hand for 30 years.

“Many tennis-playing families would not vacation anywhere else,” insists Ken Thompson, director of The Breakers’ tennis program. “We have fostered and nurtured these relationships to the point that we are now teaching the grandchildren of families we started with 25 years ago.” Where else on holiday will a pro remember that your 12-year-old son prefers a two-handed backhand and your daughter is a lefty with a wicked serve?

More than any other demographic, affluent families treasure resorts that offer something expected for every age bracket.

“Because we are a fully private island, parents take solace in the fact that their children can run or bike as far as their hearts’ desire without ever leaving the safe confines of the resort,” says Pascal Mongeau, the general manager at Parrot Cay in Turks and Caicos. “Families that return year after year have their routine down—as soon as they hit the sand the kids are off kayaking in the mangroves, going on pirate scavenger hunts with the staff or collecting conch shells on the beach.” 

Many children plant their own coconut or banana tree and make their first stop the plantation to see how much it’s grown. Annual guest Steven Novick of New Canaan, Connecticut, agrees: “Over the years, the staff has come to feel like our extended family. I know every time we come here we’re making lasting memories that will stay with the kids long after they’ve grown.” Mr. Novick’s dream is to eventually purchase a piece of the island and retire to Parrot Cay.

Standing annual reservations are as common at Stein Eriksen in Utah as they are at The Resort at Pedregal in Cabo San Lucas, where around 20 percent of Christmas-week guests have been coming back for five or more years. At the latter, yearly returnees genuinely view the resort as a home away from home: After Hurricane Odile last year, repeat guests created a fund to help employees who had lost their real homes in the storm. The most loyal guests, a family of four that has stayed at Pedregal 38 times, arrived on re-opening day, determined to be the first through the tunnel to their treasured retreat. The staff even made the mother a uniform so she could hang out at the concierge desk with her adopted holiday family. You don’t get that kind of just-one-of-us service at a hot new resort in Ibiza or Bali.

Like his fellow annual travelers, Sadler Ramsdell will know exactly what to expect when he goes back to Curtain Bluff, on the Caribbean island of Antigua, for the 25th time this winter. “I have heard it called the resort of 1,000 hugs, since when you arrive you hug all of your returning friends and of course the excellent staff,” the Pennington, New Jersey, resident says.

He and his wife invited couples they met at the upscale all-inclusive resort to their daughter’s recent wedding; this fall the Ramsdells are witnessing the union of another friend they met on holiday at Curtain Bluff. Going back year after year is almost like a reunion. “We and our children have made lifelong friends there,” Ramsdell says. With any luck, those kids will bring their kids, and three generations of Ramsdells will be basking in the thrill of familiarity every year, for decades to come.

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